Heteroleptic μ-nitrido diiron complex supported by phthalocyanine and octapropylporphyrazine ligands: Formation of oxo species and their reactivity with fluorinated compounds

作者: Cédric Colomban , Evgeny V. Kudrik , Alexander B. Sorokin

DOI: 10.1142/S1088424617500274

关键词:

摘要: The synthesis and reactivity of [Formula: see text]-bridged diiron macrocyclic complexes have been a topic of increasing interest in recent years since the observation of particular catalytic properties of these complexes. Herein, we report a preparation of a novel heteroleptic μ-nitrido diiron complex with unsubstituted phthalocyanine and octapropylporphyrazine macrocycles. This complex reacts with [Formula: see text]-chloroperbenzoic acid to form high-valent diiron oxo species showing strong oxidizing properties. The formation and structure of the transient oxo species was investigated by cryospray collision induced dissociation MS/MS technique. Analysis of fragmentation pattern showed that the attachment of oxo moiety occurred at either iron phthalocyanine or at iron porphyrazine site with slight preference for the phthalocyanine iron site. The catalytic properties of the heteroleptic μ-nitrido diiron complex were evaluated in the oxidative transformation of hexafluorobenzene and perfluoro(allylbenzene).

参考文章(53)
Joan Serrano-Plana, Isaac Garcia-Bosch, Ryosuke Miyake, Miquel Costas, Anna Company, Selective Ortho-Hydroxylation–Defluorination of 2-Fluorophenolates with a Bis(μ-oxo)dicopper(III) Species† Angewandte Chemie. ,vol. 53, pp. 9608- 9612 ,(2014) , 10.1002/ANIE.201405060
Mala A. Sainna, Debangsu Sil, Dipankar Sahoo, Bodo Martin, Sankar Prasad Rath, Peter Comba, Sam P. de Visser, Spin-state ordering in hydroxo-bridged diiron(III)bisporphyrin complexes. Inorganic Chemistry. ,vol. 54, pp. 1919- 1930 ,(2015) , 10.1021/IC502803B
Olga V. Zalomaeva, Irina D. Ivanchikova, Oxana A. Kholdeeva, Alexander B. Sorokin, Kinetics and mechanism of the oxidation of alkyl substituted phenols and naphthols with tBuOOH in the presence of supported iron phthalocyanine New Journal of Chemistry. ,vol. 33, pp. 1031- 1037 ,(2009) , 10.1039/B821534K
Graham de Ruiter, Niklas B. Thompson, Michael K. Takase, Theodor Agapie, Intramolecular C–H and C–F Bond Oxygenation Mediated by a Putative Terminal Oxo Species in Tetranuclear Iron Complexes Journal of the American Chemical Society. ,vol. 138, pp. 1486- 1489 ,(2016) , 10.1021/JACS.5B12214
Matthew G Quesne, Dhurairajan Senthilnathan, Devendra Singh, Devesh Kumar, Pascale Maldivi, Alexander B Sorokin, Sam P de Visser, None, Origin of the Enhanced Reactivity of μ-Nitrido-Bridged Diiron(IV)-Oxo Porphyrinoid Complexes over Cytochrome P450 Compound I ACS Catalysis. ,vol. 6, pp. 2230- 2243 ,(2016) , 10.1021/ACSCATAL.5B02720
Pavel Afanasiev, Alexander B. Sorokin, μ-Nitrido Diiron Macrocyclic Platform: Particular Structure for Particular Catalysis Accounts of Chemical Research. ,vol. 49, pp. 583- 593 ,(2016) , 10.1021/ACS.ACCOUNTS.5B00458
Alexander B. Sorokin, Phthalocyanine Metal Complexes in Catalysis Chemical Reviews. ,vol. 113, pp. 8152- 8191 ,(2013) , 10.1021/CR4000072
Zhiqi Cong, Haruki Kinemuchi, Takuya Kurahashi, Hiroshi Fujii, Factors affecting hydrogen-tunneling contribution in hydroxylation reactions promoted by oxoiron(IV) porphyrin π-cation radical complexes. Inorganic Chemistry. ,vol. 53, pp. 10632- 10641 ,(2014) , 10.1021/IC501737J
David F. Bocian, Eric W. Findsen, Joseph A. Hofmann, G. Alan Schick, Daniel R. English, David N. Hendrickson, Kenneth S. Suslick, Interaction of dioxygen with binuclear nitride-bridged iron porphyrins Inorganic Chemistry. ,vol. 23, pp. 800- 807 ,(1984) , 10.1021/IC00175A003